Is that the evil gnome that lives under the cubicle? Nope. It’s Brian!
Brian and I had very different experiences telling our employers about our plans to leave our jobs to travel.
My boss has known about our travel plans since 2010 when, during my annual review, she asked me:
Where do you see yourself in five years? What do you think your future with the organization looks like?
I was so caught off guard by the formal questioning that I did something I never would have normally done in this awkward situation: I told the truth.
Welllll, I stuttered, Brian and I have this dream of traveling the world. I mean, there’s a lot that needs to happen between now and then, and it’s a long way off, but I guess that’s where I see myself in five years.
Internally, even as the words were tumbling out of my mouth, I was screaming to myself: Kim! Shut up!!! What! Are! You! Doing?!?!?!
I freaked out for weeks afterwards, certain that it was just a matter of time before I was called into the office and let go.
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Since the accidental reveal, I’ve been semi-open about our plans. When we put our house on the market last summer, I told my boss it was a step towards our grand goal of travel. When we moved into our apartment, I told her we’d signed a ten-month lease and that we planned to leave when the lease was up. Then there is this blog, of course. The truth has always been just one google search away.
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Brian’s employer, on the other hand, had no idea about our plans. I might go blab, blab, blabbing and skipping about like a delusional Mary Poppins, but Brian plays his cards a little closer to his chest. He planned to give six weeks notice.
That plan was thrown out the window when the supervisory position in Brian’s work group was suddenly vacated and Brian was tagged to fill the role, at least temporarily, while they recruited to fill the job permanently. On one hand, this was good news- more money to save! A great professional opportunity for Brian! On the other hand, it was bad news- Brian’s department was now severely short-staffed. His supervisors and co-workers laid it on thick, encouraging him in not-so-subtle ways to apply for the position permanently.
It felt like the Universe was testing us. After years of crawling up the ladder, not to mention a massive fight just to get on the damn ladder in the first place, Brian had a great opportunity for professional advancement. It came at an inopportune time.
We spent weeks discussing the situation. Should he apply for the job? Should he tell his boss about our plans?
Brian decided not to apply. He felt it was dishonest to take the job knowing that he’d be leaving five months later. He also decided to keep quite about our plans, though he hated that his co-workers and supervisors assumed that he wasn’t applying because he didn’t believe himself up to the task.
The stress of the whole situation weighed on him. He hoped that they would find the perfect candidate and that he could spend his remaining time bringing the new hire up to speed. Then, when he left, he’d feel confident knowing that he’d done everything he could to leave his supervisors and co-workers in a good spot.
A few weeks later they found a good candidate and offered her the job. She turned it down.
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Now Brian was in a really bad spot.
His supervisors really pulled out all the stops this time around. Every member of the management team stopped by and told him they thought he would be good in the role. One of his supervisors told him it was fate, that the universe doesn’t normally offer second chances, and that he shouldn’t pass the opportunity up again. The other sat him down, looked him in eye and said: Please apply for the job.
He knew he had to come clean. He set up a meeting with this boss and promptly began worrying.
What if they fired him? What if they were angry at him? Even worse, what if they were disappointed? They’d invested a lot in him and he liked his job, he felt loyal to his colleagues. On top of all that, he also felt an unshakable guilt for choosing what he wanted to do- travel- over what people expected him to do- advance his career.
He didn’t sleep much in the days leading up to the meeting and was full of anxiety as he sat down with his boss. He knew she was expecting a much different conversation than the one that was about to take place.
He told her he appreciated that she wanted him in the position and he was honored that his colleagues thought so highly of him, but he wasn’t going to apply for the job. He told her that we’d dreamed for years of taking some extended time to travel and that we were finally in the position to make those dreams come true. He was happy at work, but his decision had nothing to do with work. The decision was about life and how he wanted to live it.
Brian’s boss paused briefly to organize her thoughts and then shocked Brian by what she said next.
She told him that she fully supported his decision. She still wanted him to apply for the job because, even if she only had him for four months, she’d take it. She told him that he needed to follow his dreams, that he’d never be content in his career otherwise, and that she’d do whatever she could to help him make his dreams a reality.
Then, she said she’d like to explore the option of a leave of absence. That, if on day 364 Brian didn’t want to come back, he could just call up HR and tell them so. She thought a leave of absence would give him a backup plan in case something went awry while we were on the road.
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As Brian relayed the whole story to me later in the evening (over celebratory nachos and beers, of course), I couldn’t help but notice how relaxed and happy he was. He’d finally come clean at work. Not only was the weight off his shoulders, but revealing our plans had turned out even better than he could have imagined.
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We’ve got 15 weeks of work left (67 work days, but who’s counting?) and finally (finally!) we can both talk openly about our plans. Revealing our plans has given Brian the freedom to get excited about our trip and he is diving into the planning process with an enthusiasm he didn’t quite have before.
Keeping quiet in the 9-5 feels like living a double life. I don’t think either of us really understood the kind of toll it was taking on Brian. Now that everyone knows about our plans, the reality of our adventure is really setting in.
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We're Kim and Brian and we have one goal: Sell our stuff, quit our jobs, and crawl (claw?) our way out of our cubicles to travel the world. 
Congrats!! I remember sooooo well what a relief it was to finally come clean!
Thanks Katie!!
I can fully empathise with how Brian felt. I took a job as a teacher in a school knowing that I would only stay there for one year before going travelling. A few months into term the Head of Department left and as I had HOD experience they asked me to step into the role. They offered a pay increase but as I knew they wanted somebody longer term than I could give I felt uncomfortable taking the promotion. I couldn’t tell them why I refused and spent a long time feeling guilty!!
When I finally came clean they were very supportive. They couldn’t keep a job open for me but they said I could reapply whenever I got back and they would be very happy to hire me if a vacancy arose. It’s so much better to speak honestly about plans to travel but I understand it is stressful not knowing if this could cost your job!
Hope you guys have a great time
That’s a pretty uncanny similarity! It is SO much better to be open but so hard to find that fine line between honestly and just, well, potentially setting yourself up for an early exit.
I’m glad your job was supportive
Always an awkward situation, and there is no one stock answer, but I can feel the relief Brian felt wash over him.
Congratulations!
Thank you! I could literally SEE the release of stress from him. It was weighing on him even more than he knew.
Love it, this has a great message. Employers/employees most of the time would prefer up-front honesty really.
Best of luck on your travels!
Andrew
Thanks Andrew! Yes, most of the time I’m sure they do… and yet, it is so freaking stressful trying to figure out if they do in your case. All worked out well in the end
Heya, I have just stumbled onto your page from Almost Fearless!!
So excited for you both and your upcoming travel.
I am currently in the same place as Brian has been – not being able to tell anyone about my travel plans for the fear of losing my job.
I have 2 jobs.. and if I lost either one of then I lose my dream entirely.
I cant wait till im able to finally say something to the people I work with – especially since I work in the travel industry.. however the time is so far away (August) I have to keep my plans in my head and with the friends I trust the most to not put any info out into the universe of social network or say anything infront of those who hold my future in their hands.
I even have to keep my plans hidden from my flatmates… argh… 7 Months……
Hi Manda! So glad you found us
Ugh, I completely feel your pain (and Brian certainly would too). I remember the fear of knowing that if either of us lost our job we would also be losing our ability to fund our dreams. Though, I’m sure there would be another way to get there, BUT, neither one of us wanted to figure that one out (and I know you don’t want to either!!!).
All I can say is I wish for you patience and perseverance. We have been planning this trip for years and years. Saving and saving and selling our stuff and I swear there were so many times it felt as though it would NEVER get here. I still can’t believe we are so close now. I’d like to tell you 7 months will fly by but it WON’T. It will DRRRAAAGGGG ONNNNNNN. But you will get there eventually and when you do it will be amazing
Oh I know it will drag… its dragging now and its only been a month… argh.
But in the mean time – I have your blog updates to keep me inspired!!
Argh!!! Damn the dragging! But there is so much to look forward to and anticipation is such a fun thing to have. A million good lucks to you. You! will! get! there!
wow! i applaud both of you. i’m always about the honest thing too when i’ve chosen to travel or move in the past. (i’m raising my 8 yo daughter by myself now so following all you travel greats from my armchair for now) i’m excited for you and glad everything is falling into place!enjoy – you deserve it!
Thank you so much Marina
Honesty is the best policy- good for the giver and the receiver. Much love 
Thanks for the article. I’ll be going through the same thing with my manager sometime in the next few month.
Ah, good luck to you!!
Kim, that is so awesome! I know you & Brian are hoping traveling will be an indefinite life change but it’s so amazing that his company offered up this back up plan! I’m so happy for you guys!
Hi Ali! Yes, we are hoping to travel indefinitely but, you’re right, it is nice to have a backup plan. As Brian said, it can’t hurt to have options. Thanks for your support Ali
What wonderful news, congratulations to you both! Brian particularly must be feeling both super relieved and elated!
I’ll also be quitting my job to go on a RTW trip at the end of this year, and have to say, I’m dreading, and at the same time looking forward to having ‘the talk’ with my boss. I’m mostly nervous about coming across ungrateful for / unappreciative of the opportunity I’ve been given. On the flip side, I can’t wait for the time when I will finally be able to talk openly about my adventure!
Fingers crossed I’ll find myself in a similar position to Brian in that my boss will be encouraging of my attempt at a different way of life!
Oh, I completely hear you about the fear of coming across as ungrateful. I think that if you just tell your boss how grateful you are, she will see. I think that most people don’t begrudge you your dreams. I know that I always make sure to tell my boss how grateful I am that she allows me to talk openly about our plans because it would be so hard for me to ‘lead the double life.’ I really am thankful that she allows me to plan this next step knowing that it has nothing to do with working for her organization.
Wow! That is fantastic!!!!
Thanks Amy, it was such an unexpected surprise!
That is such great news! I definitely can empathize, I had a similar experience before moving to Zagreb..when I finally told my boss, it was such a huge weight lifted off my shoulders. Now, I’m happy at my new job here but my fiance and I dream of moving onto the next country. Since everything is still so up in the air, it’s hard to commit to anything at my new job when I want to start applying for jobs in other countries! Anyway, congrats and I’m looking forward to reading more from you both
It’s funny because I asked Brian, at the height of his anxiety, if he would be feeling so horrible about telling his boss if he was leaving to take another job instead of leaving to travel. He said that he didn’t think he would be as worried. A lot of his anxiety was coming from choosing to do something that he really wanted to do (travel) instead of something that he felt he should do (work). Either way, it’s a freaking stressful conversation to have with the boss!
Although we’re way far away from our travels, that story gives me a little bit of hope. When I was still a temp here, I asked for a meeting with my boss and told him I wanted to apply. He said he was relieved because the whole time he was just waiting for me to tell him I had found another job. He’s incredibly supportive and I know he’ll be ok with it once I tell him (far, far off in the future), but I know he’ll be disappointed. I guess, really, it’s a good thing though.
Also, I noticed Brian’s cubicle is pretty bare like mine. I have little to no personal stuff in it and you wouldn’t believe the amount of flack I get for that.
I’ve been people’s boss before- and I’ve had people quit on me to take other jobs or explore other opportunities. It stinks, but it’s not the earth shattering devastation that we believe we are delivering as the one’s who are leaving, you know? Our bosses are human, just like us.
Yep, I guess B never really “moved in” to his cube
That sounds like a very tough situation for Brian to handle, but it all turned out well in the end. It sounds like the excitement that it’s really, really going to happen is settling in! Pretty soon you won’t be living a double life, but the life you really want to live
I hope the 15 weeks fly by!
I hope the 15 weeks fly by too!!!! You guys should know I am going to be obsessing over the countdown in every post
That is amazing!! Oh, those Portland bosses, so much more understanding than others
Haha, we are pretty laid back over here on the west coast
Congrats on both of you guys revealing your RTW travel plans to employers!
Reading through this reminds me of how primarily negative bosses/employers can be to people who have the slightest thought of going after their dreams. Yea, of course businesses are simply thinking of long-term ramifications of having to replace a employee … but with all the negativity in the world … people have to be supportive of each other’s dreams.
Hi Harrison. In our case, we found that both of our bosses were supportive- luckily. Brian did have a funny experience with a peer that just could not understand why he wouldn’t want to apply for the supervisor position. Brian started getting a lot of negativity from this person because this guy is just super ambitious and couldn’t understand that someone would choose a personal over professional goal. To each his own, I suppose.
Oh my goodness – thank you so much for writing this. It is exactly what I needed right now as I’m devising my plan to come clean in the next two weeks or so. I realize no two people’s experiences are ever going to be the same, but it does give me a little bit of hope. Most importantly, it is a great reminder of how great I will feel when the weight is lifted, no matter what the outcome.
Sarah, good luck!! You are guaranteed to feel lighter and freer once you come clean
Woohoo!!! One more hurdle cleared!!! So happy for you guys – people surprise you sometimes don’t they?
Yes, sometimes they do
Exciting times ahead!
I still remember when I had to tell my employer that we were leaving indefinitely. It was so awkward. BUT, 2 years later, they hired me back… so I got to eat my cake too!
Niiiice Cam. That certainly worked out for the best!
This was one of our biggest sources of stress leading up to our trip too! Huge weight off of our shoulders when we could freely talk with everyone about our plans! So glad to hear everyone was so supportive!
Thanks Caroline! It was definitely a blessing that everything worked out as it did.
Kim,
Oh my gosh! I so hear you! I’ve been feeling like I have this crazy dual personality for quite some time now. It’s crazy. I am a terrible liar to begin with so it makes it all the worse. Ugh! Hopefully not much longer but, as you know, everything takes longer than you wish it did.. We are loving watching your adventure and, as it is looking like you will be setting off first, we will be cheering you from the sidelines. Best, @TheBigBreak
Thank you for the cheers. We are cheering for you too.
I am also a horrible liar which is why I wasn’t completely surprised when the truth just came tumbling out of me. It just feels so wrong to live the double life! But, also, sometimes it is necessary until you are at the right point to come clean. Good luck
I hope it does happen as soon as it can.
Wow, is there anything bad about Portland? Even your bosses are awesome! Well done guys, another hurdle you have sailed over. I can’t wait to tell my boss I’m leaving – I literally have to force myself not to quit on an almost daily basis. It will be one sweet moment
Savour yours xxx
Hehe, Portland is pretty great!
I gotta admit, I am just a tiny bit sad that I didn’t get to have that sweet “I’m quitting” moment that you sometimes conjure up after a long day of work!
I’m chiming in on this convo…yes, Portland is pretty great.
But, having had the opportunity to give the big middle finger to a former employer I couldn’t wait to get away from…I couldn’t do it. I wanted to walk in and say, “I QUIT!” quite defiantly, and instead I spoke so softly the president could hardly hear me. I had repeat myself. Granted, I was leaving for another job and not fulfilling some wonderful dream, but…I always think it’ll more grand than it really is. Eventually it still felt pretty damn good. Too bad at that time I didn’t know the job I’d be going to was going to suck so badly.
Yay!! Yay, yay, yay. I’m so excited for you two. I know exactly the sensation of that huge sigh of relief — that sense of freedom after coming clean about plans that will steer life away from other people’s expectations… Hugs to you!
Thank you Bethany!!! Yes, I’m sure you guys definitely know the feeling. Tell Ted we said Happy Birthday
Exciting times ahead guys! You’ve made me a follower and I look forward to seeing where your travels take you.
Thank you Will. Much appreciated
Hi Kim (and Brian)! As usual, awesome post!
I remember that feeling so well. Leading the double life. Being so excited on one hand and feeling so guilty on the other. Feeling like a liar. Having the career advancement conversations, the we-love-you-now-how-to-best-develop-you conversations, the scheduling 6 months ahead, the feeling of deceit. It was so hard to tell my boss, I went in shaking like a leaf. But just like Brian, I felt so much better when it was finally done.
I think the anticipation is always worse than the actually event. I’m glad you held your head high and pulled it off
It’s just one of those things we’ve all got to get through (in this situation) to make it to the other side.
Great story! The beginning sounds all too familiar. It’s a shame that companies (speaking of US-based companies in general) aren’t more open to allowing employees to take leaves. Allowing people to take extended time away from work often results in greater productivity (long term) and company loyalty.
Thomas, I completely agree. It’s too bad there isn’t more flexibility. Not only do you have more productive and loyal employees, but you also have better educated employees who will know a bit about the world.
Congratulations guys! Have been reading your blog for awhile but I’ve never commented here before – Brian your hard work really paid off. You deserved it mate!
Thank you!! Lots of hard work and now the time is finally upon us (well, almost). SO SOON! Thanks for following along
Congrats and good luck! Wish you the best.
Thanks Stephen!
Thank you SO MUCH for this post. I work in Television and have had to keep completely silent about our RTW plans. I’ve known since May 2011 and will only be able to tell them June 2012 that I’m leaving on this trip. It’s extremely stressful not being able to share anything and constantly lying! But boy oh boy do you make me look forward to coming clean! What a relief it’ll be! Great post!
It’s soooo stressful, I really do feel for you. It’s true that it feels like a double life. Good luck in June. You will feel AMAZING and FREE!!!
Congrats to both of you, now that the whole truth is finally “out”! How awesome for Brian that his boss was so supportive!!!
I haven’t found myself in the same position, really, but last year when I won a semi-sponsored trip to New Zealand, I was really worried about approaching my boss (and his boss) about taking 2 weeks of unpaid time off in order to go. I’d already used up all my vacation time, and was planning to quit in a few months to go back to school. I figured they’d be angry and think me silly for wanting to take MORE time off to travel. But, instead, everyone was so supportive and impressed that I was able and willing to so quickly plan a trip halfway around the world. I was really lucky!
Yay!!! If you win a trip to New Zealand you’ve got to take it- work or no work! As this thing keeps unfolding I’ve found that people just continue to surprise me with their support and kind words of encouragement. My coworkers are wonderful- asking me about the trip and even planning a party for us. And everyone tells me that now is the time to do it. ‘Do it while you’re young!’, they say. It just reiterates the fact that this is the right decision.
Great post, the truth is excellent employees are very hard to find. Hiring an unknown personality for an organization is a risky proposition at the best of times. We’ve had many employees over the years and there are some that have left that we would hire back in a heartbeat. I suspect that you are both the kind of people employers are on the prowl for. Congrats on getting it all out in the open.
Thanks Daniel. It does feel fabulous to have it all out in the open. It also feels wonderful, especially for Brian, to feel so valued.